Water → 1-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-3-bromopropane

HRID 842579Notes

Reaction equation

HRID 842579 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.C(=O)([O-])[O-].[K+].[K+].[Cl:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH:21]=[C:22]([Cl:24])[Cl:23])[CH:16]=[C:15]([Cl:25])[C:14]=1[OH:26].O>CN(C)C=O>[Cl:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH:21]=[C:22]([Cl:24])[Cl:23])[CH:16]=[C:15]([Cl:25])[C:14]=1[O:26][CH2:4][CH2:3][CH2:2][Br:1]

Participants

6

Reactant 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenol

Product 1

HCID 108840691-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-3-bromopropaneYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A reaction vessel was charged with 10.6 g of 1,3-dibromopropane, 5.53 g of potassium carbonate and 100 ml of N,N-dimethylformamide, to which a solution of 30.5 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol dissolved in 40 ml of N,N-dimethylformamide was slowly added dropwise. After stirring at room temperature for 24 hours, the reaction mixture was poured into water, and extracted twice with 150 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 11.1 g of 3,5-dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (77% yield), nD24.0 1.5693.

Workup

  1. additionwas slowly added dropwise
  2. extractionextracted twice with 150 ml of diethyl ether
  3. washThe combined ether layer was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto obtain a crude product

Sources & evidence

ORD record
ord-99e8d991b26149d48155f6244ffaffc6
Source dataset
uspto-grants-2002_04
Patent number
US06376428B1

Reaction notes

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